Schedule & results
| Date | Opponent | Site | Score | Record | Event | ||
|---|---|---|---|---|---|---|---|
| Fri, Aug 27, 1999 | Corbin | away | W | 16–7 | 1-0 | ||
| Fri, Sep 3, 1999 | South Dearborn, IN | away | W | 20–0 | 2-0 | ||
| Fri, Sep 10, 1999 | Ryle | home | L | 23–38 | 2-1 | ||
| Fri, Sep 17, 1999 | Boone County | home | L | 13–21 | 2-2 | ||
| Fri, Oct 1, 1999 | Holmes | home | L | 25–28 | 2-3 | District game | |
| Sat, Oct 9, 1999 | Covington Catholic | away | W | 10–0 | 3-3 | District game | |
| Fri, Oct 15, 1999 | Scott | away | W | 32–6 | 4-3 | District game | |
| Fri, Oct 22, 1999 | Dixie Heights | home | L | 9–27 | 4-4 | District game | |
| Fri, Oct 29, 1999 | Highlands | away | L | 10–47 | 4-5 | District game |
